2-(5,5-二甲基-1,3,2-二氧硼杂烷-2-基)苯甲酸乙酯 | 346656-34-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(5,5-二甲基-1,3,2-二氧硼杂烷-2-基)苯甲酸乙酯
• 中文别名: 2-(5,5-二甲基-1,3,2-二氧杂环己硼-2-基)苯甲酸乙酯
• 英文名称: ethyl 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
• CAS: 346656-34-6
• 化学式: C₁₄H₁₉BO₄
• 分子量: 262.113
• InChiKey: GZHASWCTAWNFFW-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.63
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 储存条件：
  保存方法：将它们存放在冰箱内。

SDS

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Section I.Chemical Product and Company Identification
Chemical Name Ethyl 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzoate
Portland OR
Synonym Benzoic acid, 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-,
ethyl ester (CA INDEX NAME);
2-(2-Carbethoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborinane;
2-(2-Ethoxycarbonylphenyl)-5,5-dimethyl-1,3,2-dioxaborinane;
2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzoic Acid
Ethyl Ester
Chemical Formula C14H19BO4
346656-34-6
CAS Number

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
Ethyl 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 346656-34-6 Min. 98.0 (T) Not available. Not available.

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Section III. Hazards Identification
Acute Health Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Ingestion
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Not available.
May be combustible at high temperature. Auto-Ignition
Flammability
Flash Points Flammable Limits Not available.
Not available.
These products are toxic carbon oxides (CO, CO2). Borates.
Combustion Products
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
Ethyl 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzoate

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Section VI. Accidental Release Measures
Spill Cleanup Heat sensitive material.
Absorb with an inert material and put the spilled material in an appropriate waste disposal. Finish cleaning the spill by rinsing
Instructions
any contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
disposal.

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Section VII. Handling and Storage
HEAT SENSITIVE. REFRIGERATE.
Handling and Storage
Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a dry, cool
Information
place. Avoid excessive heat and light. Do not breathe gas/fumes/ vapor/spray.
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Provide exhaust ventilation or other engineering controls to keep the airborne concentrations of vapors below their respective
Engineering Controls
threshold limit value. Ensure that eyewash station and safety shower is proximal to the work-station location.
Splash goggles. Lab coat. Vapor respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
Personal Protection
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Liquid. (Clear. Pale yellow - reddish Solubility
Physical state @ 20°C Not available.
yellow.)
Not available.
Specific Gravity
Molecular Weight 262.11 Partition Coefficient Not available.
Boiling Point Not available. Not available.
Vapor Pressure
Melting Point Not available. Vapor Density Not available.
Not available. Not available.
Refractive Index Volatility
Critical Temperature Not available. Odor Not available.
Not available. Not available.
Viscosity Taste

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Section X. Stability and Reactivity Data

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Stability
Conditions of Instability Avoid excessive heat and light.
Incompatibilities Reactive with oxidizing agents.

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Section XI. Toxicological Information
RTECS Number Not available.
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Not available.
Toxicity Data
CARCINOGENIC EFFECTS : Not available.
Chronic Toxic Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
No specific information is available in our data base regarding the toxic effects of this material for humans. However,
Acute Toxic Effects
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling this
compound.

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Section XII. Ecological Information
Ecotoxicity Not available.
Environmental Fate Not available.
Continued on Next Page
Ethyl 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzoate

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Section XIII. Disposal Considerations
Waste Disposal Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
Not a DOT controlled material (United States).
DOT Classification
PIN Number Not applicable.
Proper Shipping Name Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not controlled under WHMIS (Canada).
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements Not available.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

HSL-IN-3（示例42）是一种硼酸衍生物，它是激素敏感性脂肪酶的抑制剂。

反应信息

• 作为反应物：
  描述：

  2-(5,5-二甲基-1,3,2-二氧硼杂烷-2-基)苯甲酸乙酯 在 四(三苯基膦)钯 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 potassium phosphate 、 2,4,6-三氯苯甲酰氯 、 三乙酰氧基硼氢化钠 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 生成
  参考文献：
  名称：

  基于HSP90抑制剂radicicol的大环化合物合成路线的开发

  摘要：

  短路线被报告给新的大环内酯（例如，9，12，20）与所述HSP90抑制剂根赤壳菌素。

  DOI：

  10.1016/j.tetlet.2006.01.116
• 作为产物：
  描述：

  水杨酸乙酯 在 2-吡啶甲酸 、 potassium phosphate 、 copper(l) iodide 、 氯化镍二甲氧基乙烷 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 2-(5,5-二甲基-1,3,2-二氧硼杂烷-2-基)苯甲酸乙酯
  参考文献：
  名称：

  镍催化的芳基和苄基2-吡啶基醚的硼化反应：转化稳固的邻位导向基团的方法

  摘要：

  描述了镍通过2-吡啶氧基的损失催化的芳基2-吡啶醚的硼化反应。该方法允许将2-吡啶氧基用作CH键官能化反应中的可转换导向基团。镍催化剂还可以使芳基甲基2-吡啶基醚硼化，对于手性仲苄基底物，其中苄基位置的立体化学得以保留。

  DOI：

  10.1002/adsc.201600336

文献信息

• Synthesis of Ortho Substituted Arylboronic Esters by in Situ Trapping of Unstable Lithio Intermediates
  作者：Jesper Kristensen、Morten Lysén、Per Vedsø、Mikael Begtrup

  DOI：10.1021/ol015598+

  日期：2001.5.1

  using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr)(3)) is a highly efficient and experimentally straightforward process for the preparation of ortho substituted arylboronic esters. The mild reaction conditions allow the presence of functionalities such as ester or cyano groups or halogen substituents that are usually not compatible with the conditions used

  [反应：参见正文]使用2,2,6,6-四甲基哌啶锂（LTMP）与三异丙基硼酸酯（B（OiPr）（3））结合进行原位锂化是一种高效且实验简单的制备方法取代的芳基硼酸酯的制备。温和的反应条件允许存在官能团，例如酯或氰基或卤素取代基，这些官能团通常与在芳烃的定向邻位金属化中使用的条件不兼容。芳基硼酸酯与多种芳基卤化物进行了铃木型交叉偶联，以53-94％的收率提供了联芳基。
• Synthesis and metallation of 2-(pyridyl)benzoic acids and ethyl 2-(pyridyl)benzoates: a new route to azafluorenones
  作者：Anne-Sophie Rebstock、Florence Mongin、François Trécourt、Guy Quéguiner

  DOI：10.1016/s0040-4020(03)00761-0

  日期：2003.6

  The ring deprotonation of 2-(2- and 4-pyridyl)benzoic acids using lithium dialkylamides in THF at rt, and the in situ cyclization afforded 4- and 2-azafluorenones, respectively. 1-Azafluorenone was obtained from ethyl 2-(3-pyridyl)benzoate using a similar protocol.

  使用二烷基氨基锂在rt在THF中对2-（2-和4-吡啶基）苯甲酸进行环去质子化，并进行原位环化，分别得到4-和2-氮杂芴酮。使用类似的方案，从2-（3-吡啶基）苯甲酸乙酯获得1-氮杂芴酮。
• An Asymmetric Aerobic Aza-Wacker-Type Cyclization: Synthesis of Isoindolinones Bearing Tetrasubstituted Carbon Stereocenters
  作者：Guoqiang Yang、Chaoren Shen、Wanbin Zhang

  DOI：10.1002/anie.201203693

  日期：2012.9.3

  It's all in the solvent: An enantioselective variant of an aza‐Wacker‐type cyclization that gives isoindolinones containing tetrasubstituted carbon centers α to the nitrogen atom has been developed (see scheme; tfa=trifluoroacetate). The use of a highly coordinating solvent is crucial for the activity of the catalyst and the stereoselectivity the reaction (up to 99 % ee).

  一切都在溶剂中：已经开发出aza-Wacker型环化的对映体选择性变体，该变体可将含四取代碳中心α的异吲哚啉酮带至氮原子（参见方案； tfa =三氟乙酸盐）。使用高度配位的溶剂对于催化剂的活性和反应的立体选择性（至多99％ee）至关重要 。
• Synthesis of substituted diazino[c]quinolin-5(6H)-ones, diazino[c]isoquinolin-6(5H)-ones, diazino[c]naphthyridin-6(5H)-ones and diazino[c]naphthyridin-5(6H)-ones
  作者：Nathalie Fresneau、Thomas Cailly、Frédéric Fabis、Jean-Philippe Bouillon

  DOI：10.1016/j.tet.2013.04.104

  日期：2013.7

  Substituted diazino[c]quinolin-5(6H)-ones and -isoquinolin-6(5H)-ones, diazino[c]naphthyridin-6(5H)- and -5(6H)-ones were obtained using two synthetic routes: one-pot cross-coupling/cyclisation and two-step cross-coupling/KOH-mediated anionic ring closure. The two strategies gave yields in the same order of magnitude and their choice depends on the availability of the starting material.

  使用以下方法获得取代的重氮[ c ]喹啉-5（6 H）-one和-异喹啉-6（5 H）-one，重氮[ c ]萘啶-6（5 H）-和-5（6 H）-one。两种合成途径：一锅交叉偶联/环化和两步交叉偶联/ KOH介导的阴离子闭环。两种策略产生的收率处于相同的数量级，其选择取决于起始物料的可用性。
• Indeno[1,2‐ <i>b</i> ]fluorene‐Based [2,2]Cyclophanes with 4 <i>n</i> /4 <i>n</i> and 4 <i>n</i> /[4 <i>n</i> +2] π Electrons: Syntheses, Structural Analyses, and Excitonic Coupling Properties
  作者：Chi‐Shin Wang、Yu‐Chen Wei、Kai‐Hsin Chang、Pi‐Tai Chou、Yao‐Ting Wu

  DOI：10.1002/anie.201903561

  日期：2019.7.22

  11)indeno[1,2‐b]fluorenophane and its precursor [2.2](5,11)indeno[1,2‐b]fluorene‐6,12‐dionophane exhibit remarkable transannular interactions, leading to their unusual electrochemical and photophysical properties. With the aid of femtosecond transient absorption spectroscopy, the transition from the monomeric excited state to the redshifted H‐type dimeric state was first observed, correlating to the calculated

  制备了具有4 n / 4 n和4 n / [4 n +2]π电子系统的基于茚并[1,2 - b ]芴的[2,2]环烷，并通过X射线晶体学对其结构进行了鉴定。当π-π距离短于3.0Å时，[2.2]（5,11）茚并[1,2- b ]芴酮及其前体[2.2]（5,11）茚并[1,2- b]]芴-6,12-二氟环烷表现出显着的跨环相互作用，从而导致其异常的电化学和光物理性质。借助飞秒瞬态吸收光谱法，首先观察到了从单体激发态到红移H型二聚体态的跃迁，这与计算出的激子能量分裂和电荷转移介导的超交换引起的稳态吸收谱相关相互作用。